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Search results; Over 1,000 homes in Oakland

Guest favourite
Hut in Oakland
Large estate, miles of trails, cozy hut Stanley
1 bedroom, 4 beds, 6 private bathrooms
12–17 Sept, Business host
,
4.88 out of 5 average rating, 90 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.86 out of 5 average rating, 29 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 169 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 189 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
4.92 out of 5 average rating, 119 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 121 reviews
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds, 1 bathroom
7–12 Dec
5.0 out of 5 average rating, 117 reviews
Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
Top guest favourite
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 145 reviews
Guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.95 out of 5 average rating, 57 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
12–17 Sept
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews